CN102807773B - Blue dye composition, and dyeing application of blue dye composition on fiber - Google Patents
Blue dye composition, and dyeing application of blue dye composition on fiber Download PDFInfo
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- CN102807773B CN102807773B CN201210271646.4A CN201210271646A CN102807773B CN 102807773 B CN102807773 B CN 102807773B CN 201210271646 A CN201210271646 A CN 201210271646A CN 102807773 B CN102807773 B CN 102807773B
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- 0 CC(C1)C(C(c(cc2)ccc2Nc2ccc(*)cc2)=C(C=C2)C=CC2=[N+](*)Cc2cc(S(O)(=O)=O)ccc2)=CC=C1N(*)Cc1cccc(S(O)(=O)=O)c1 Chemical compound CC(C1)C(C(c(cc2)ccc2Nc2ccc(*)cc2)=C(C=C2)C=CC2=[N+](*)Cc2cc(S(O)(=O)=O)ccc2)=CC=C1N(*)Cc1cccc(S(O)(=O)=O)c1 0.000 description 2
Abstract
The invention provides a blue dye composition and a dyeing application of the blue dye composition on fibers. The dye composition comprises one or more dye compounds represented by the following general formula (1) and one or more dye compounds represented by the following general formula (2). Each dye compound represented by the general formula (1) is triarylmethane acidic dye; the triarylmethane acidic dye is gorgeous and bright in color and high in developing property, is widely used for dyeing natural and synthetic polyamides, leathers and papers, but is poor in sunshine resistance and fastness to washing, so that the promotion and the application are affected seriously. Compared with the dye compounds represented by the general formula (1), the blue dye composition provided by the invention not only maintains the characteristics of gorgeous color and brightness but also obviously enhances and improves the fastness, thereby satisfying the current printing and dyeing requirements.
Description
Technical field
The present invention relates to a kind of blue dyes composition and the tint applications on filamentary material thereof.Particularly, the present invention relates to a kind of blue dyes composition and the tint applications on natural and synthetic polyamide fiber thereof.
Background technology
The present invention is intended to research and develop a kind of blue dyes composition natural and synthetic polyamide fiber dyeing that is applied to.
One of component of the blue dyes composition the present invention relates to, as shown in general formula (1), is a class triarylmethane dyes.This class dyestuff just put into production as far back as the twenty or thirty age in last century.This class dyestuff is bright-coloured with coloured light, color developing is strong, easy to make being good at, thereby be widely used in the dyeing of animal and plant fiber, leather, paper.The still production in a large number of current Chinese matching stain factory, satisfies the demands.But have to point out, this class dyeing fastness is poor, is embodied in the fastness such as photostabilization, thermotolerance, humidity resistance and water tolerance poor.This class dyeing fabric is not washable, the defect of sun-proof not, has a strong impact on its application.
The emphasis of current triarylmethane dyes development research is:
1, adopt new triarylmethane Leuco to prepare the oxidizing process of triaryl methane matching stain developing body, reduce and decontamination, and reduce costs.
2, dissimilar laking agent is selected in research, improves the colour fastness of triarylmethane dyes.
The inventor, in improving the research of triarylmethane dyes colour fastness, is surprised to find that the matching stain and the triarylmethane dyes blending that adopt other chemical classes, can significantly improve its colour fastness.
The inventor is on the basis of lot of experiments research, find to adopt the represented triaryl methane type matching stain blending of the represented acid anthraquinone dye of general formula (2) and general formula (1) pleasantly surprisedly, not only keep the feature that coloured light is bright-coloured, tint permanence is strong, and its colour fastness is all significantly improved.
The inventor confirms, adopts the matching stain blending of other chemical types of colour fastness excellence, is the effective way of improving triarylmethane dyes dyeing behavior.
Summary of the invention
The inventor is on the basis of a large amount of research trials, find pleasantly surprisedly, the dye composite that one or more triaryl methane type blue dyess that one or more blue anthraquinone type dyes that general formula (2) represents and general formula (1) represent form, has gorgeous, the excellent dyeing behavior of coloured light and every fastness.
Pleasurable, the low defect of colour fastness of the triaryl methane type blue dyes that general formula (1) represents, by dye composite of the present invention, is significantly improved, and still keeps coloured light gorgeous, the feature that color developing is strong.
The inventor confirms, adopts the matching stain blending of other chemical types of colour fastness excellence, is one of effective way of improving triarylmethane dyes dyeing behavior.
The dye composition that the dye composition that one or more general formulas (1) shown in being selected from below that blue dyes composition provided by the invention comprises that certain proportion mixes represent and one or more general formula (2) shown in being selected from below represents.
In formula:
R
1, R
2, R
3and R
4be H, C independently respectively
1-4alkyl or
group;
R
5and R
6be H or C independently respectively
1-4alkyl;
R
7for
-NR
9r
10or-SO
3m;
R
8for H, C
1-4alkyl or C
1-4alkoxyl group;
R
9and R
10be H, C independently respectively
1-4alkyl or phenyl;
R
11for H or-SO
3m;
N is 2 or 3 integers;
M is H or alkali metal cation;
In formula:
M is 0,1,2 or 3;
P is 0 or 1;
M is H or alkali metal cation;
R
12for-NHCOCHXCH
2x or-NHCOCX=CH
2group
Wherein X is Cl or Br.
The present invention also provides the tint applications of above-mentioned blue dyes composition in natural and synthetic polyamide fiber and BLENDED FABRIC thereof.
Embodiment
Dye composite of the present invention comprises the dye composition of one or more general formulas (1) expression and the dye composition that one or more general formulas (2) represent.
In dye composite of the present invention, the dye composition that general formula (1) represents (being called for short dyestuff I) is 95-5:5-95, preferably 80-20:20-80 with the weight ratio of the dye composition (being called for short dyestuff II) that general formula (2) represents.
One preferred embodiment in, the R in general formula (1)
1, R
2, R
3and R
4group, when they are independently
during group, wherein-SO
3be positioned on benzene nucleus-CH of M group
2position or contraposition between-group.
Another preferred embodiment in, the R in general formula (1)
7group, when it is
during group, R wherein
8contraposition, a position or the ortho position of be positioned on benzene nucleus-NH-group of group.
One preferred embodiment in, the SO in general formula (1)
- 3and/or SO
3m is positioned on the contained phenyl ring of dye composition that general formula (1) represents.
One preferred embodiment in, (the CH in general formula (2)
3)
mgroup, works as m=3 ,-CH
3ortho position and the contraposition of lay respectively on benzene nucleus-NH-group of group; Work as m=2 ,-CH
3contraposition, a position or the ortho position of lay respectively on benzene nucleus-NH-group of group; Work as m=1 ,-CH
3ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group of group.
Another preferred embodiment in, the R in general formula (2)
12group, ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group; In general formula (2)-SO
3m group, ortho position, a position or the contraposition of when p=1, be positioned on benzene nucleus-NH-group.
One preferred embodiment in, in general formula (1) and general formula (2),
R
1, R
2, R
3and R
4be H, C independently respectively
1-4alkyl or
group;
R
5and R
6be H, C independently respectively
1-4alkyl;
R
7for
-NR
9r
10or-SO
3m;
R
8for H, C
1-4alkyl or C
1-4alkoxyl group;
R
9and R
10be H, C independently respectively
1-4alkyl or phenyl;
R
11for H or-SO
3m;
R
12for-NHCOCHXCH
2x or-NHCOCX=CH
2group; Wherein X is Cl or Br.Another preferred embodiment in, in general formula (1) and general formula (2),
N is 2 integers;
M is 0,1 or 3 integers;
P is 0 or 1;
M is H or alkali metal cation.
Above-mentioned C
1-4alkyl for example comprises methyl, ethyl, propyl group or butyl, above-mentioned C
1-4alkoxyl group for example comprises methoxyl group, oxyethyl group, propoxy-or butoxy, and above-mentioned alkali metal cation for example comprises sodium or potassium ion.
In the present invention, the dye composition that general formula (1) represents, for example, comprise following example:
In the present invention, the dye composition that general formula (2) represents, for example, comprise following example:
Dyestuff II-8.
The dye composition that the dye composition that general formula (1) is represented and general formula (2) represent is known dye.
The synthetic method of the dye composition that general formula (1) represents, can consult following patent and paper:
US 1218232(1917)(Max Weiler)
US 1731637(1929)(General Aniline Works)
US 4330476(1982)(Bayer)
JP 53074530 (1978) (Baotugu Chemical Industrial Co., Ltd)
Pan Guoguang, triaryl methane series matching stain synthetic, dyestuffs industries Vol 30 (5), 11-20 (1993)
Pan Guoguang, the synthetic and application on dyestuffs industries of 4-chloro-benzaldehyde, dyestuffs industries, Vol 28(6), 24-28 (1991)
Fourth Jinchang, Pan Guoguang, the improvement of acid gorgeous blue G synthesis technique, Journal of Wenzhou Normal College (natural science edition), 6,63-65(1995)
The synthetic method of the dye composition that general formula (2) represents, can consult following patent and paper:
CN 101585974(2009) (Tianjin Dek Chemical Company Ltd.)
CN 101177544(2008) (Shangyu Xincheng Chemical Industry Co., Ltd., Zhejiang Longsheng Group Co., Ltd., Zhejiang Province Longsheng Group Co., Ltd)
Pan Mingchu, containing synthesizing of 4-sym-trimethylbenzene aminoanthraquinone dyestuff, dyestuffs industries, Vol 38, (3), 9-14(2001)
Zhu great Quan, the study on the synthesis of C.I. ACID BLUE 129, Shanghai dyestuff Vol 28, (6), 18-21 (1999)
Sun Fenglong etc., the research of C.I. ACID BLUE 129 process for cleanly preparing, dyestuff and dyeing Vol 46(5), 25-27(2009)
The Representative Cultivars of the dye composition that general formula (2) represents---C.I.Acid Blue's 225 is synthetic, can consult above-mentioned CN 101585974(2009) (Tianjin moral is triumphant), the raw material M acid in patent is replaced into diamino sym-trimethylbenzene.
Blue dyes composition of the present invention also can contain the dye additive of various conventional uses in dyeing and dye formulations, and its consumption can be selected according to actual needs, and there is no particular limitation, is generally no more than 20 % by weight.For example, electrolyte salt, as sodium sulfate or Repone K, content 0～10 % by weight, preferably 2～6 % by weight; PH adjusting agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0～5 % by weight, preferred 0.5～2.5 % by weight, dust-proofing agent 0～10 % by weight, preferred 0.1～2 % by weight; Solubility promoter 1～15 % by weight, preferred 0.1～3 % by weight.The present composition also can be substantially by general formula (1) dyestuff of above-mentioned weight ratio with general formula (2) dyestuff forms or be comprised of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio.
The preparation method of blue dyes composition of the present invention comprises above-mentioned general formula (1) dyestuff and general formula (2) dyestuff weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as mechanically mixing method.During mixing, general formula (1) dyestuff and general formula (2) dyestuff can powder types, or with particle form, or exist with aqueous solution form.For example, mixing step can suitable shredder as ball mill or needle mill in and in kneader or mixing machine, carry out.
Blue dyes composition of the present invention is suitable for dyeing and various materials widely thereof.
Blue dyes composition of the present invention can be applied to filamentary material and be fixed on fiber by several different methods as known in the art, for example, can dye by dip-dye method or printing method.
Embodiment
Every testing method of embodiment
The properties of the present embodiment is tested by following every testing method
1, solubleness: take a certain amount of dyestuff in the beaker of 250ml, add the hot water of 80 ℃ of 100ml, carry out suction filtration (during suction filtration, pressure 0.075Mpa, 5A qualitative filter paper) with mechanical stirrer stirring after 5 minutes, observe filter paper residual condition.Reduce dye strength (G/L), until residual without dyestuff on filter paper, dye strength now (G/L) is the solubleness of dyestuff.
2, dyeing nylon exhaustion rate test: dye liquor preparation, by the acid dyeing dyeing of nylon.After dyeing finishes, test respectively the absorbancy of dyeing residual liquid and the absorbance of the front dye liquor of dyeing.
Exhaustion rate=(absorbance of the front dye liquor of absorbance/dyeing of dye liquor after 1-dyeing) * 100%
3, colour fastness to chlorinated water test: by dyeing nylon fabric, measure by international standard ISO 105E03.
4, colour fastness to perspiration test: dyeing nylon fabric, through fixation treatment, is measured by international standard ISO 105-E04.
5, fastness to soaping test: dyeing nylon fabric, through fixation treatment, is measured by international standard ISO 105-C10.
6, sunlight fastness test: by dyeing nylon fabric warp, measure by 20 hours conditions of international standard AATCC 16E.
Dye type shown according to the form below 1 and consumption thereof evenly mix various dye components by ordinary method in this area, the various anthraquinone type Vickery blue compositions of the preparation embodiment of the present invention.
" % " in table 1 all represents % by weight, and the gross weight of dye composite of take is benchmark.
Table 1
| Numbering | Dyestuff title | Form |
| 1 | A | 10% dyestuff I-1+90% dyestuff II-1 |
| 2 | B | 20% dyestuff I-1+80% dyestuff II-1 |
| 3 | C | 40% dyestuff I-1+60% dyestuff II-1 |
| 4 | D | 60% dyestuff I-1+40% dyestuff II-1 |
| 5 | E | 20% dyestuff I-2+80% dyestuff II-3 |
| 6 | F | 30% dyestuff I-2+70% dyestuff II-3 |
| 7 | Reference X | 100% dyestuff I-1 |
| 8 | Reference Y | 100% dyestuff II-1 |
Embodiment 1
The coloured light of blue dyes composition of the present invention
The coloured light of blue dyes composition of the present invention is bright-coloured sapphirine, and bright-colored degree is high, and enhancing is good, and being applicable to, in the dyeing and printing process of all kinds of bright color textiless, has higher actual application value.
Embodiment 2
Solubleness test
The solubleness that is determined as follows as stated above dyestuff, test result is recorded in table 2
Table 2
From table 2:
Blue dyes composition of the present invention, has good solubleness, and level-dyeing property is better.
Embodiment 3
Dyeing nylon exhaustion rate is measured
The exhaustion rate that is determined as follows as stated above dyestuff, test result is recorded in table 3
Table 3
From table 3:
Blue dyes composition of the present invention there is splendid dyeing exhaustion rate.
Embodiment 4
Chlorinated water resist fastness
The colour fastness to chlorinated water that is determined as follows as stated above dyestuff, test result is recorded in table 4
Table 4
From table 4:
Blue dyes composition of the present invention still has excellent chlorinated water resist fastness.
Embodiment 5
Colour fastness to perspiration
The colour fastness to perspiration that is determined as follows as stated above dyestuff, test result is recorded in table 5
Table 5
From table 5:
Blue dyes composition of the present invention, has good fastness to perspiration compared with reference X dyestuff.
Embodiment 6
Fastness to soaping
The fastness to soaping that is determined as follows as stated above dyestuff, test result is recorded in table 6
Table 6
From table 6:
Blue dyes composition of the present invention, compared with reference X dyestuff, has good fastness to soaping.
Embodiment 7
Sunlight fastness
The colour fasteness to sunlight that is determined as follows as stated above dyestuff, test result is recorded in table 7
Table 7
From table 7:
Blue dyes composition of the present invention has greatly improved the poor defect of dyestuff sunlight fastness that general formula (1) represents.
Claims (10)
1. a blue dyes composition, this dye composite comprises the dye composition that dye composition that one or more general formulas (1) shown in being selected from below represent and one or more general formula (2) shown in being selected from below represents:
In formula:
R
1, R
2, R
3and R
4be H, C independently respectively
1-4alkyl or
group;
R
5and R
6be H or C independently respectively
1-4alkyl;
R
7for
-NR
9r
10or-SO
3m;
R
8for H, C
1-4alkyl or C
1-4alkoxyl group;
R
9and R
10be H, C independently respectively
1-4alkyl or phenyl;
R
11for H or-SO
3m;
N is 2 or 3 integers;
M is H or alkali metal cation;
In formula:
M is 0,1,2 or 3;
P is 0 or 1;
M is H or alkali metal cation;
R
12for-NHCOCHXCH
2x or-NHCOCX=CH
2group;
Wherein X is Cl or Br;
The weight ratio of the dye composition that the dye composition that general formula (1) represents and general formula (2) represent is 95～5:5～95.
2. blue dyes composition claimed in claim 1, is characterized in that, the weight ratio of the dye composition that the dye composition that general formula (1) represents and general formula (2) represent is 80～20:20～80; SO in general formula (1)
- 3and/or SO
3m is positioned on the contained phenyl ring of dye composition that general formula (1) represents.
3. blue dyes composition claimed in claim 1, is characterized in that, the R in general formula (1)
1, R
2, R
3and R
4group, when they are independently
during group, wherein-SO
3be positioned on benzene nucleus-CH of M group
2position or contraposition between-group.
4. blue dyes composition claimed in claim 1, is characterized in that, the R in general formula (1)
7group, when it is
during group, R wherein
8contraposition, a position or the ortho position of be positioned on benzene nucleus-NH-group of group.
5. blue dyes composition claimed in claim 1, is characterized in that, (the CH in general formula (2)
3)
mgroup, works as m=3 ,-CH
3ortho position and the contraposition of lay respectively on benzene nucleus-NH-group of group; Work as m=2 ,-CH
3contraposition, a position or the ortho position of lay respectively on benzene nucleus-NH-group of group; Work as m=1 ,-CH
3ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group of group.
6. blue dyes composition claimed in claim 1, is characterized in that, the R in general formula (2)
12group, ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group; In general formula (2)-SO
3m group, ortho position, a position or the contraposition of when p=1, be positioned on benzene nucleus-NH-group.
7. blue dyes composition claimed in claim 1, is characterized in that, in general formula (1) and general formula (2),
N is 2;
M is 0,1 or 3 integers;
P is 0 or 1;
M is H, sodium or potassium ion.
8. blue dyes composition claimed in claim 1, is characterized in that, the dye composition that general formula (1) represents is:
9. blue dyes composition claimed in claim 1, is characterized in that, the dye composition that general formula (2) represents is:
In claim 1～9 the blue dyes composition described in any one in the tint applications of natural and synthetic polyamide fiber and BLENDED FABRIC thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210271646.4A CN102807773B (en) | 2012-08-01 | 2012-08-01 | Blue dye composition, and dyeing application of blue dye composition on fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210271646.4A CN102807773B (en) | 2012-08-01 | 2012-08-01 | Blue dye composition, and dyeing application of blue dye composition on fiber |
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| Publication Number | Publication Date |
|---|---|
| CN102807773A CN102807773A (en) | 2012-12-05 |
| CN102807773B true CN102807773B (en) | 2014-04-02 |
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ID=47231650
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105385189A (en) * | 2015-11-30 | 2016-03-09 | 无锡新德印染制品有限公司 | Blue reactive dye composition |
| CN105968876A (en) * | 2016-06-30 | 2016-09-28 | 叶文佳 | Compound type reactive dye formula |
| CN107460602B (en) * | 2017-09-13 | 2020-08-11 | 利郎(中国)有限公司 | Production process of four-side stretch fabric |
Citations (6)
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|---|---|---|---|---|
| US2657205A (en) * | 1950-01-09 | 1953-10-27 | Hoechst Ag | Dyes containing a vinyl sulfone |
| US4330476A (en) * | 1979-07-13 | 1982-05-18 | Bayer Aktiengesellschaft | Preparation of cationic triarylmethane dyestuffs |
| EP1013719A1 (en) * | 1998-12-22 | 2000-06-28 | Ciba SC Holding AG | Process for trichromic dyeing or printing |
| CN101585974A (en) * | 2008-12-12 | 2009-11-25 | 天津市德凯化工有限公司 | Method for preparing wool reactive-dye brilliant blue |
| CN101864195A (en) * | 2009-04-16 | 2010-10-20 | 明德国际仓储贸易(上海)有限公司 | Dye composition |
| CN102604428A (en) * | 2012-01-19 | 2012-07-25 | 上海雅运纺织化工股份有限公司 | Anthraquinone type blue acidic dye composition and its application in fibers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5374530A (en) * | 1976-12-14 | 1978-07-03 | Hodogaya Chem Co Ltd | Preparation of triarylmethane acidic dye |
| JPS58125755A (en) * | 1982-01-21 | 1983-07-26 | Sumitomo Chem Co Ltd | Anthraquinone-type anionic dye composition |
-
2012
- 2012-08-01 CN CN201210271646.4A patent/CN102807773B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2657205A (en) * | 1950-01-09 | 1953-10-27 | Hoechst Ag | Dyes containing a vinyl sulfone |
| US4330476A (en) * | 1979-07-13 | 1982-05-18 | Bayer Aktiengesellschaft | Preparation of cationic triarylmethane dyestuffs |
| EP1013719A1 (en) * | 1998-12-22 | 2000-06-28 | Ciba SC Holding AG | Process for trichromic dyeing or printing |
| CN101585974A (en) * | 2008-12-12 | 2009-11-25 | 天津市德凯化工有限公司 | Method for preparing wool reactive-dye brilliant blue |
| CN101864195A (en) * | 2009-04-16 | 2010-10-20 | 明德国际仓储贸易(上海)有限公司 | Dye composition |
| CN102604428A (en) * | 2012-01-19 | 2012-07-25 | 上海雅运纺织化工股份有限公司 | Anthraquinone type blue acidic dye composition and its application in fibers |
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|---|---|
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Effective date of registration: 20171201 Address after: 215400, Binhai Road, Taicang Port Development Zone, Taicang port, Jiangsu, Suzhou 16, China Patentee after: Suzhou Kefaman Chemical Co. Ltd. Address before: 201812 Shanghai city Xuhui District Yindu Road No. 388 building 16 275-278 Patentee before: Shanghai Argus Textile Chemical Co., Ltd. |